Many methods have been known for a long time for halogenation of organic compounds. As a halogenating agent in these, halogen simple substances, hydrogen halides, or halogen-containing phosphorus or sulfur compounds are well used. However, these halogenating agents are problematic in point of their safety as they are toxic. In particular, since the environmental load in treating their wastes is large these days, use of these halogenating agents on an industrial scale may be difficult in future.
Various halogen-containing compounds are known, which have characteristic properties derived from the halogen atom therein. Above all, many fluorine-containing compounds have specific physiological activities and functions, and their applications in various fields are under investigation. In particular, the importance of fluorine-containing compounds in the filed of medicines, agricultural chemicals and the like is increasing more and more.
Few fluorine-containing compounds exist in nature, and it is necessary to introduce fluorine atom to the compound by organosynthetic method. Accordingly, industrially-useful fluorinating agents and fluorination methods with a low environmental load are strongly desired, and their studies and developments are being made in many aspects.
Recently, novel fluoroamine compounds have been developed, which can selectively fluorinate a functional group with oxygen, sulfur, halogen or the like and which are thermally stable, low-toxic and easily handlable have been developed (e.g., see Patent Reference 1). One typical compound of the type is N,N-diethyl-α,α-difluoro-(3-methylbenzyl)amine. This compound changes back, after used for fluorination of a substrate, to N,N-diethyl-meta-toluamide, which is a starting compound for this compound; and its excellent advantageous is that the toluamide can be recovered and reused.
However, N,N-diethyl-meta-toluamide has a high boiling point and is a good solvent by itself, and therefore it is hard to say that the recovery of the compound is easy, as the compound is well soluble with various organic compounds. As a result, the energy consumption in the entire process increases, and the wastes increase; and therefore the method is not satisfactory in point of the environmental load.
Recently, studies of green chemistry for the purpose of reducing the environmental load have become active, and development of ecological processes is one important theme in the art. For example, a polymer-supported halogenating agent and the like has been developed in consideration of recovery and recycle of starting material (e.g., see Patent References 2 and 3).
On the other hand, a field of fluorous chemistry of which the studies have just begun in these ten several years is specifically noted from the viewpoint of green chemistry. Fluorous chemistry is an art using the property of highly-fluorinated fluoro compounds that are hardly soluble in ordinary organic solvents and water but are readily soluble in fluorous solvents (fluorous property) (e.g., see Non-Patent References 1 and 2). The fluorous property may be given to compounds by introducing a fluorous-tag (perfluoro group) into them; however, a fluorinating agent with such a fluorous-tag introduced thereinto and its production method, and an ecological fluorination method using it are unknown.    Patent Reference 1: WO03/020685    Patent Reference 2: JP-A 2000-154155    Patent Reference 3: JP-A 2002-293828    Non-Patent Reference 1: Makoto Misonoo, the Journal of Organic Synthetic Chemical Society of Japan, 61, 406 (2003)    Non-Patent Reference 2: Ryu Ilhyong, Hiroshi Matubara, Chemistry, 57, 20 (2002)